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Cheap flights from Chicago Midway Airport to San José from $154

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 10/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Multiple Airlines Logo
5:28 pm - 10:41 amMDW-SJO
18h 13m1 stop
Multiple Airlines Logo
4:50 pm - 11:25 pmSJO-MDW
29h 35m2 stops
$320Multiple Airlines
Find Deal
Fri, Oct 17 - Wed, Oct 22
Multiple Airlines Logo
6:26 pm - 11:40 pmMDW-SJO
29h 14m2 stops
Multiple Airlines Logo
9:00 am - 9:22 pmSJO-MDW
12h 22m1 stop
$330Multiple Airlines
Find Deal
Tue, Nov 11 - Sat, Nov 15
Delta Logo
6:00 am - 11:58 amMDW-SJO
6h 58m1 stop
Delta Logo
1:23 pm - 10:14 pmSJO-MDW
7h 51m1 stop
$340Delta
Find Deal
Tue, Oct 21 - Fri, Oct 24
Delta Logo
10:47 am - 10:07 pmMDW-SJO
11h 20m1 stop
Delta Logo
2:31 pm - 11:32 pmSJO-MDW
9h 01m1 stop
$344Delta
Find Deal
Wed, Nov 19 - Tue, Nov 25
Southwest Logo
8:45 pm - 11:20 amMDW-SJO
15h 35m2 stops
Southwest Logo
12:35 pm - 10:35 pmSJO-MDW
9h 00m1 stop
$345Southwest
Find Deal
Fri, Oct 3 - Wed, Oct 8
Delta Logo
6:48 pm - 10:07 pmMDW-SJO
27h 19m2 stops
Delta Logo
7:00 am - 4:39 pmSJO-MDW
9h 39m1 stop
$348Delta
Find Deal
Mon, Nov 17 - Mon, Nov 24
Southwest Logo
5:50 am - 1:15 pmMDW-SJO
7h 25m1 stop
Southwest Logo
9:00 am - 10:35 pmSJO-MDW
13h 35m2 stops
$349Southwest
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Thu, Nov 6 - Tue, Nov 11
Multiple Airlines Logo
12:28 pm - 6:45 pmMDW-SJO
31h 17m2 stops
Multiple Airlines Logo
8:50 am - 11:46 pmSJO-MDW
13h 56m1 stop
$350Multiple Airlines
Find Deal
Fri, Oct 10 - Mon, Oct 13
Frontier Logo
6:00 am - 1:43 pmMDW-SJO
7h 43m1 stop
Frontier Logo
2:58 pm - 11:26 pmSJO-MDW
8h 28m1 stop
$354Frontier
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Sat, Jan 10 - Sat, Jan 17
Frontier Logo
6:00 am - 1:43 pmMDW-SJO
7h 43m1 stop
Frontier Logo
2:58 pm - 11:26 pmSJO-MDW
8h 28m1 stop
$364Frontier
Find Deal
Wed, Jan 7 - Sat, Jan 17

Delta flights from Chicago Midway Airport to San José, San José Province

Our best Delta deals on Chicago Midway Airport to San José, San José Province flight tickets
Delta
Oct 21
MDW6:00 amChicago Midway
6h 58m
1 stop
SJO11:58 amSan José Juan Santamaria Intl
Oct 24
SJO1:23 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:14 pmChicago Midway
$340
Find similar
Delta
Nov 19
MDW10:47 amChicago Midway
11h 20m
1 stop
SJO10:07 pmSan José Juan Santamaria Intl
Nov 25
SJO2:31 pmSan José Juan Santamaria Intl
9h 01m
1 stop
MDW11:32 pmChicago Midway
$344
Find similar
Delta
Nov 17
MDW6:48 pmChicago Midway
27h 19m
2 stops
SJO10:07 pmSan José Juan Santamaria Intl
Nov 24
SJO7:00 amSan José Juan Santamaria Intl
9h 39m
1 stop
MDW4:39 pmChicago Midway
$348
Find similar

Southwest flights from Chicago Midway Airport to San José, San José Province

Our best Southwest deals on Chicago Midway Airport to San José, San José Province flight tickets
Southwest
Sep 30
MDW6:25 amChicago Midway
13h 30m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Oct 3
SJO1:30 pmSan José Juan Santamaria Intl
10h 15m
1 stop
MDW12:45 amChicago Midway
$340
Find similar
Southwest
Oct 3
MDW8:45 pmChicago Midway
15h 35m
2 stops
SJO11:20 amSan José Juan Santamaria Intl
Oct 8
SJO12:35 pmSan José Juan Santamaria Intl
9h 00m
1 stop
MDW10:35 pmChicago Midway
$345
Find similar
Southwest
Nov 6
MDW5:50 amChicago Midway
7h 25m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
Nov 11
SJO9:00 amSan José Juan Santamaria Intl
13h 35m
2 stops
MDW10:35 pmChicago Midway
$349
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José, San José Province that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San José, San José Province that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 10/17

5:28 pm-10:41 am

1 stop18h 13m

San José Juan Santamaria Intl

Wed 10/22

4:50 pm-11:25 pm

2 stops29h 35m

$320

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 11/11

6:26 pm-11:40 pm

2 stops29h 14m

San José Juan Santamaria Intl

Sat 11/15

9:00 am-9:22 pm

1 stop12h 22m

$330

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 10/21

6:00 am-11:58 am

1 stop6h 58m

San José Juan Santamaria Intl

Fri 10/24

1:23 pm-10:14 pm

1 stop7h 51m

$340

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 11/19

10:47 am-10:07 pm

1 stop11h 20m

San José Juan Santamaria Intl

Tue 11/25

2:31 pm-11:32 pm

1 stop9h 01m

$344

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 10/3

8:45 pm-11:20 am

2 stops15h 35m

San José Juan Santamaria Intl

Wed 10/8

12:35 pm-10:35 pm

1 stop9h 00m

$345

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 11/17

6:48 pm-10:07 pm

2 stops27h 19m

San José Juan Santamaria Intl

Mon 11/24

7:00 am-4:39 pm

1 stop9h 39m

$348

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 11/6

5:50 am-1:15 pm

1 stop7h 25m

San José Juan Santamaria Intl

Tue 11/11

9:00 am-10:35 pm

2 stops13h 35m

$349

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 10/10

12:28 pm-6:45 pm

2 stops31h 17m

San José Juan Santamaria Intl

Mon 10/13

8:50 am-11:46 pm

1 stop13h 56m

$350

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 1/10

6:00 am-1:43 pm

1 stop7h 43m

San José Juan Santamaria Intl

Sat 1/17

2:58 pm-11:26 pm

1 stop8h 28m

$354

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 1/7

6:00 am-1:43 pm

1 stop7h 43m

San José Juan Santamaria Intl

Sat 1/17

2:58 pm-11:26 pm

1 stop8h 28m

$364

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José, San José Province

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San José, San José Province?

The month of August is, on average, the cheapest month to fly to San José, San José Province from Chicago Midway Airport, with most prices found around $477. If you’re not able to fly to San José, San José Province in August, then September is your next best option. Flight prices from Chicago Midway Airport to San José, San José Province during September average around $477.

What is the cheapest day to depart on your flight to San José, San José Province?

The cheapest day to depart from Chicago Midway Airport to San José, San José Province is on a Tuesday when prices can be found for as low as $541. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $815.

What is the cheapest time of day to depart on your flight to San José, San José Province?

In the evening is the cheapest time of day to fly from Chicago Midway Airport to San José, San José Province when you can find flight prices for as low as $453. Flying to San José, San José Province in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to San José, San José Province, so prices are often more expensive at around $763 per ticket.

When to book flights from Chicago Midway Airport to San José, San José Province

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José, San José Province according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José, San José Province (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José, San José Province

Direct flights

None
There are no direct flights from Chicago Midway Airport to San José, San José Province. There are no popular flight routes from Chicago Midway Airport to San José, San José Province.
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  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 55m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José, San José Province?

Best airlines flying from Chicago Midway Airport to San José, San José Province

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José, San José Province with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $394Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Alajuela
Monteverde
Heredia
Dominical
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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